Blue trisazo dye.



* No Drawing.

human srnrns PATENT ornron;

HEINRICH J ORDAN AND WILHELM'NEELMETER, OF LEVERKUSEN, NEAR COLOGNE,

GERMANY, ASSIGNORS TO FARBENFABRIKEN VORM. FRIEDR. BAYER & G0,, 0]?

ELBERFELD, GERMANY, A oonronnrro'n or sun-MANY. I

BLUE TRISAZO DYE.

To all whom it may concern:

Be it known that we, HEINRICH JOB-DAN and ZILHELM N EELMEIER, doctors of ph losophy, chemists, citizens of the German Em-i pire, residingat Leverkusen, near'Cologne, Germany, have invented new and useful Improvements in Blue Trisazo Dye, of which the following is a specification. v

The present invention relates to the manufacture and production of new azo dyestuflis which are obtained bycombining the diazo compounds prepared from ti-amino- 2-acidylamino-l -phenol ethers of the for (R meaning an alkyl, e. 9. methyl or ethyl, R meaning a substituent, such as chlorin, 'alkyl) with 1-naphthylamin-6- or 7-sultonic acid (or a mixture of these acids), rediazotizing the aminoazo compounds thus obtained,combining the diazoazo compounds with a second molecule of one of these acids (or of a mixture of the same), rediazotizin-g the aminodisazo compounds thus produced and combining the diazodisazo com ounds with a-naplithol sulfonic acid, especia ly 1.3- and 2.7-naphthol sulfonic acid and finally eliminating the acidyl radical by sa'ponification. Blue cotton dyestufis are thus obtained; they are after being dried and pule verized dark powders soluble in water generally with. a blue coloration. Upon treatment with stannous chlorid and hydrochlorio acid they are split up, a 2.5-diaminobenzene derivative of the formula amin'onaphthol sulfonic acid are obtained. They can be diazo -ized on the fiber and developed e. g. with'beta-naphthol the result being bright shades of excellent fastness to specification of Letters Patent.

Patented Dec. 5. 1911.

Application filed January 4, 1911. Serial No. 600,818.

washing which can'he discharged withhydrosulfite to a pure white.

f In order to illustrate the new process more fully the/following example is given, the

parts being by weight: 245 parts of 2-o2zalylaminol-chloro-5-amino-l-anisol oer-i I y -,nn-oo-ooon lTH2 4 a are dissolved in 7000 parts of water with the addition of parts of sodium carbonate and are after acidulation with350 parts of hydrochloric acid (19 B.) diazotized at about 1520 O. with 69 parts of sodium nitrite. The diazo solution is combined with a solution of 245 parts of lnaphthylaminfisult'onic acid (sodium salt) containing 220 parts of acetate of sodium (100 per cent),

the combination takes place within a few minutes. The nnxtureus rendered alkaline,

mixed with 69 parts of sodium nitrite and then diazotized by adding at 1015 C/the requisite quantity of hydrochloric acid. The

diazotizationis complete after stirring for 1 to 2 hours and the resulting diazo compound is then again combined in theprcsence of 280 parts of sodium acetate with l-naphthyl amin-G-sulfonic acid which requires a stir ring'of the mixture for about 12 hours at 10l5 C. The second intermediate product is filtered, dissolved in 10,000 parts of water containing 70 oarts of sodium carbonate.

69 parts of so ium nitrite are added and finally after cooling to Zero sufficient hydrochloric acid to produce diazotization. The diazodisazo compound which separates as a sandy powder is added to an aqueous solution cooled to 0C. of 246 parts of l-naphthol-3-sulfonic acid (sodium salt) containing an excess of carbonate of sodium. The dye is precipitated with salt, filtered, redissolved and then heated to boilin for about 10 minutes with 1600 parts of TWaOH- (30 per cent.) to eliminate the acidyl group.

Afterv cooling to 70 C. sulfuric or hydrochloric acid is added. to neutralize the excess of caustic soda and the dye is then isolated in the usual manner. It is after being dried and pulverized a dark powder soluble in water with a blue coloration and yielding upon reduction with stannous chlorid and hydrochloric acid 2.5-diamino-4-chl0ro 1- anisol, 1.4 naphthylenediamin 6 sulfonic acid and 1-11aphthol-2-amino-3-sulfonic acid. It dyes cotton in blue shades, which when diazotized on the fiber and developed with beta-naphthol change into a greenish-blue of excellent fastness to washing and to light. It can be discharged to a pure white with hydrosulfite.

Instead of 2-oxalylamino-4-chloro-5-amino-l anisol other acidyl compounds, e. g. 2- formylamino--methyl-5-amino-1-anisol or the corresponding phenetols etc. can be used, and instead of 2.7-naphthol sulfonic acid the 1.3-naphthol sulfonic acid, and instead of the 1.6-, the 1.7 -naphthylamin sulfonic acid or a mixture of the 1.6- with the 1.7 naphthylamin sulfonic acid may be used.

1. The herein described tri sazo dyestuffs obtainable from a compound of the formula.

NHa it in which formula R means an alkyl group and R, a substituent, which dyestufis are after being dried and'pulverized dark powders soluble in water generally with a blue coloration; yielding upon treatment with stannous chlorid and hydrochloric acid a 2.5 dia-minobenzene derivative, 1.4 naphthylenediamin sulfonic acid and an amino naphthol sulfonic acid; which dyes can be diazotized on the fiber and developed with beta-naphthol giving bright shades of excellent fastness to washing which can be discharged with hydrosulfite to a pure white, substantially as described.

2. The herein described new trisazo dyestufi obtainable from a compound of the formula two molecules of l-naphthylamin-6-sulfonic acid and l-napthol-d-sulfonic acid, which dyestufi' is afterbeing dried and pulverized a dark powder soluble in water with a blue coloration; yielding upon reduction with stannous chlorid and hydrochloric acid 2.5- diamin0--chloro-l-anisol, IA-naphthylenediamin-(i-sulfonic acid and Lnaphtholamino-3-sulfonic acid; dyeing cotton in blue shades, which when diazotized on the fiber and developed with beta-naphthol change into a greenish-blue which can be discharged to a pure white with hydrosulfite, substantially as described.

In testimony whereof we have hereunto set our hands in the presence of two sub.- scribing witnesses.

HEINRICH JORDAN. a 5. WILHELISI NEELMEIER. [n s.]

Witnesses CHAS. J. WRIGHT, ALFRED HENKEL. 

